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Multistep Synthesis and Nematicidal Activity of 2-(8-azabicyclo[3.2.1]octan-3-yl)-3-imino-2,3-dihydro-1H-isoindol-1-One Derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

Novel 2-(8-azabicyclo[3.2.1]octan-3-yl)-3-imino-2,3-dihydro-1H-isoindol-1-ones derived from 5-HT3 receptor antagonists hexahydroazepinylbenzamides were designed and synthesized through isocyanide insertion reaction. All target compounds were evaluated against pinewood nematodes B. xylophilus and root-knot nematodes M. incognita. Good lethal rate (75%) for 3-(tert-butylimino)-5-chloro-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one and serious nervous curl effect against pinewood nematodes B. xylophilus for 3-(tert-butylimino)-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one were observed at 10 mg/l. The inhibition activities of 3-[(4-methoxyphenyl)imino]-2-(8-methyl-8-azabicyclo[3.2.1]octan-3-yl)-2,3-dihydro-1H-isoindol-1-one against root-knot nematodes M. incognita were 84% at 160 mg/l and 60% at 20 mg/l for in vitro test and test tube test, respectively.

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Authors and Affiliations

  1. School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, Shanghai, 200237, China

    Jun Xu, Tianjiao Yang, Jiayi Wang & Gonghua Song

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  1. Jun Xu
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  2. Tianjiao Yang
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  3. Jiayi Wang
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  4. Gonghua Song
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Correspondence to Gonghua Song.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(1), 31–39

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Xu, J., Yang, T., Wang, J. et al. Multistep Synthesis and Nematicidal Activity of 2-(8-azabicyclo[3.2.1]octan-3-yl)-3-imino-2,3-dihydro-1H-isoindol-1-One Derivatives. Chem Heterocycl Comp 57, 31–39 (2021). https://doi.org/10.1007/s10593-021-02864-z

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